


The Riding Lesson

by KoreArabin



Category: Sherlock Holmes & Related Fandoms, Sherlock Holmes: A Game of Shadows (2010)
Genre: Bondage, Crossdressing, Double Domming, F/M, Femdom, Humiliation, Humour, M/M, Nudity, Spanking
Language: English
Status: In-Progress
Published: 2013-04-22
Updated: 2013-04-30
Packaged: 2017-12-09 05:42:20
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 3,876
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/770652
Author URL: https://archiveofourown.org/users/KoreArabin/pseuds/KoreArabin
Summary: <blockquote class="userstuff">
              <p>It started with a dare.  Colonel Sebastian Moran discovered he liked wearing ladies' underwear.  The Professor decides to take matters a little further.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This arose from a particularly hilarious online convo with tiger-moran and VictorianGothic. And there can never be too much crossdressing Sebastian Moran fanfic, evah, IMNSHO.

“My dear, you are quite the artist. He looks wonderful.” 

Sebastian squirms in his chair as the Professor lays his hands on his shoulders, their touch seemingly far warmer on his skin than normal, bereft as he is of his habitual wool and linen. The soft, barely rustling silk wrapped around his upper body has his nerve-endings pulsing as if they are on fire, the tight corset constricting his waist only fuelling the burning sensation. Is this how the fair sex feel on a daily basis - restricted, _bound_ , even, quivering beneath their finery with pent up energy and emotion?

“You should see yourself, Colonel. Miss Winter has done a truly admirable job of painting your face.” With this, the Professor nods to Kitty, who has been standing by with a box of cosmetics, cloths and brushes, and a most amused expression on her face. Placing the box to one side, she picks up the ladies' vanity mirror and holds it up for Sebastian, who scowls at her from under his eyebrows before reluctantly turning his eyes to the glass.

“Fuck me! Beggin’ your pardon, Kitty, but what in the name of buggery have you done to me?”

“Colonel! Language! You will apologise to Miss Winter immediately.” Moriarty squeezes his shoulder in warning.

Sebastian grumbles. “Very sorry, Miss Kitty. I’m sorry for my bad language, and I hope it ain't offended you.”

Kitty smiles. “Thank you for your apology, Colonel. Given our long acquaintance, I have over the years grown somewhat accustomed to the rough old campaigner in you, and so I am not offended, rather - _astonished_ \- that such language should have come from so very pretty a mouth!”

Sebastian surveys himself gloomily in the hand glass. His skin is much paler than usual, the face powder also obscuring most of his freckles, but his cheeks are redder, their colour exaggerated with rouge. His lips are even brighter, stained a dark, vivid red, and his eyes are outlined with kohl, more of which has been brushed on to his lashes. Even Sebastian can see that the darkness around his eyes serves to accentuate their blue brightness, whilst the red of his lips lends him an aspect of rather dangerous, carnal, sensuality.

“You look quite delectable, my dear Colonel. Does he not, Miss Winter?”

“What? I look like a _bloke_ wearin’ make up! I’ve got a bloody _beard_ , for God’s sake!”

“Which the charming lace veil will cover most admirably, my dear. Come, Sebastian, now that the talented Miss Winter has put the final touches to your appearance, it is time for your riding lesson.”


	2. Chapter 2

As with many things in his life that Sebastian has later come to regret, it began with a dare. A silly, simple, dare by the Professor, in one of his more playful moods. A dare that Sebastian would not be able to take a message to the telegraph office whilst wearing ladies’ drawers under his trousers. 

How or why the Professor had acquired such a voluminous pair of lace-trimmed silk _knickers_ he cannot recall, but he remembers only too well the gleam in Moriarty’s eye as he held them out to him, daring him to take them and put them on.

oOo

“Don’t be shy, chick. You can put them on in here. If any of the servants come by, they know to knock before entering.”

Somewhat reluctantly, Sebastian kicks off his boots and unbuttons his fly and braces, removing his trousers and underwear in one smooth movement. The cool silk of the drawers feels alien against his skin as he pulls them up over his legs, and he feels goose pimples rising. His grunt of surprise as he pulls them up to fasten them at his waist prompts a chuckle from the Professor.

"Yes, chick. They are the old fashioned ones. Truly a _pair_ of drawers, no less."

Sebastian is hardly an expert on womens' underwear, yet he knows, from a great deal of personal experience, that the open crotched drawers of his youthful assignations have more recently given way to far more respectable closed knickers, more's the pity. The mutually enjoyable quick mount/dismount encounters with the fair sex, where the only items of clothing to be adjusted were his fly buttons, have now become a far more elaborate affair involving too many fastenings. His teenage self would probably have exploded with frustration before the object of his desire had even managed to unbutton her underwear, let alone remove it.

But, _these_ are truly _drawers_ , open at the crotch, simply disappointing in one way (he was looking forward to the sensation of cool, soft, silk against his cock and balls), but something of concern in another. Throughout his life, Sebastian has enjoyed the luxury of underwear. Whether cotton, linen or flannel, his nether regions have always been protected from the harsh scratchiness of his outer garments. The prospect of allowing his most precious organs to chafe against the rough tweed of his trousers is not one he relishes. 

"But..."

"No 'buts', chick. You accepted the challenge, and therefore it is time to walk to the telegraph office. This telegram is _most_ pressing, and I therefore suggest that you pull on your trousers and get on with it, my dove."


	3. Chapter 3

Sebastian spends the walk to the telegraph office in an agony of frustrated arousal. On the one hand, he is mortified to think of being discovered wearing silk drawers under his suit, even though the chances of anyone doing so must be infinitesimally small. However, it seems to him that his shame must be written across his face in burning letters, and the telegraph clerk and the respectable married ladies waiting in the queue can tell at a glance that they have a knicker-wearing pervert in their midst.

Yet, at the same time, the feeling of his cock and balls hanging unsupported against the seam of his trousers, and the brush of the cool silk around his genitals and on his backside as he walks, make him extremely glad that he opted to wear an overcoat over his suit for this outing. The respectable ladies in the telegraph office would most definitely be scandalised if they caught sight of Sebastian’s raging erection straining against the crotch of his trousers.

On his return to the house, the Professor is sitting at his desk writing, but looks up as Sebastian enters, his lips pressed together in barely suppressed amusement. 

“Ah, Colonel! How went your little outing? Most enjoyable for you, I should imagine? I shall have to draw up a list of errands for you to run for me.”

“If you must know, _Sir_ , it was bloody excruciating. Walking around with your bloody undercarriage danglin' out ain’t all that comfortable, and it’s bloody draughty, too.”

The Professor cannot prevent himself snorting in amusement. “My poor lamb – your _undercarriage_? Shall I examine it for you? Or perhaps we should send for the doctor? It would no doubt be a welcome distraction for the poor chap, from his usual round of runny noses and blocked bowels, to examine a chafed and chilly _undercarriage_! He might even write it up for The Lancet….”

“No bloody way, Sir! I ain’t having no bloody sawbones poking around down there! Sod that for a game of soldiers!”

“Dear me, Sebastian, your mouth is running away with you today. So much bad language, my dove, that I feel some chastisement is called for. Remove your jacket and trousers and come here.”

Somewhat reluctantly, Sebastian obeys, flushing with embarrassment as he stands before the Professor, clad only in his shirt and the silk drawers. His cock is still semi-erect, and the inside of his thigh is sticky with pre-ejaculate. 

“Over my lap, chick. Perhaps a spanking will remind you to curb your tongue in future, hmmm?”

“No, please, Sir. It’s too – too…”

“Too _what_ , my dove? Speak up!”

“Too _humiliating_ , Sir. Being spanked. Wearing ladies’ drawers.”

“Which is the _point_ of the exercise, Colonel. Chastisement is not meant to be enjoyable. Now, no more prevarication. Come here and over my lap – now, if you please!”

Sebastian cannot recall ever being forced in to a more humiliating position, his backside tilted upwards as he settles himself over the Professor’s lap. Moriarty moves him slightly, so that his feet are off of the floor, and makes him clasp his hands together in the small of his back, with the overall effect that Sebastian feels completely off balance and totally exposed.

Moriarty runs his hands over Sebastian’s silk clad buttocks, squeezing and pinching, enjoying the involuntary twitches and gasps he provokes from his prone marksman. Running his fingertips lightly over Sebastian’s exposed perineum and testicles produces a muffled groan, and Sebastian moves in his lap, trying to ease the pressure on his now fully erect cock.

“You really do look quite delightful like this, Colonel. The contrast between your firm, muscular, rump and these silky, flimsy undergarments is quite delicious. I think I shall order some more for you to wear for me – yes – I should very much like to see you in a pair of lace trimmed French knickers, in sapphire blue silk, I think, to match your eyes. Hmmm. And why stop there? How would you take to being laced into a corset, chick, I wonder, or to wearing silk stockings and garters? We shall see. But, for now…”

Sebastian yelps as Moriarty brings his hand down hard on to his left buttock. “For now you will count out the strokes of your punishment, and thank me after each one, and ask politely for the next. And know that if any are counted incorrectly, then we shall start again at the beginning. So, Colonel?”

“One! Thank you Sir. May I please have another?”


	4. Chapter 4

Sebastian is brought back from his reminiscing to the present rather abruptly, Kitty stifling a giggle as the Professor prods his backside with a hat pin. "Are you still with us, Colonel?"

"Yes, Sir. Sorry, Sir, just thinkin' is all."

"Well then, let us go. The ostler will meet us at Rotten Row with the horses, and I have arranged for a mount for you too, Miss Winter. A very handsome, yet docile, dapple grey gelding. I should deem it an honour if you will ride with us today."

Kitty inclines her head. "I shall be delighted, my dear Professor Moriarty. And I would not miss the Colonel's first foray into riding _sidesaddle_ for all the world."

oOo

Sebastian spends the carriage ride to Hyde Park staring gloomily out of the carriage window. When the Professor summoned him to his study that morning, he had at first been delighted to see Kitty there; their assocation goes back a long way and, even though they are no longer lovers (Sebastian now finds it difficult to believe that he had such a roving eye and such a wide range of casual sexual partners before he met the Professor), he still enjoys her company very much. Having always been a somewhat reserved and private man, Kitty's vivaciousness, intelligence, and sheer _joie de vivre_ never fail to captivate him.

But, this morning even Kitty's sweet face and quick wit could not prevent his stomach sinking when he caught sight of the shimmering dark green silk dress draped over the sofa. 

oOo

"My dear Colonel, today will be a day of new experiences for you. I have just been telling Miss Winter what pleasure you take in wearing ladies' drawers beneath your suit. What was it you said? The cool silk moving against your most intimate parts is so very pleasurable that you cannot believe that the fair sex are able to do anything but take to their beds and..."

"Sir! Please - no more!" Sebastian flushes crimson with mortification. How can the Professor embarrass him so, and before the lovely Kitty, of all people?

"Oh hush, Sebastian. Even though your blushes are most _becoming_ , you know that I have always liked a man who knows his mind and follows his appetites, and convention be damned! It is one of the qualities that so attracted me to you when we were - _intimate_ \- and so I must say that I _relish_ the opportunity to behold you in a state of some _excitement_ when you see what the dear Professor has prepared for you."

Sebastian takes Kitty's hand and kisses it. Bless her, and her generosity of spirit. Very many women would be aghast at learning of his relationship with Moriarty, and even more so at what Sebastian regards as his perverse enjoyment of the soft ladies' underthings. Kitty is, however, thankfully not most women, and he feels again the great affection that he had and, indeed, still has, for her.

The Professor looks on in fond amusement. His Sebastian is so very chivalrous, and so very innocent, in so many ways, and these qualities simply add to his enjoyment of their games. And so, with a mock sternness that he does not really feel, but adds to the excitement his dove experiences when submitting to him, he growls, "Strip."


	5. Chapter 5

"But - but - umm - Miss Kitty, Sir?"

"Yes, Colonel? Is this gaping imitation of a goldfish for Miss Winter's benefit?"

"No, Sir. Umm, what? No, but undressin' before the _lady_ , Sir."

At this, Kitty laughs, a bright, silver sound, which has Sebastian flushing deeply again. "Oh, Sebastian, what a silly boy you are! The good Professor knows of our association, dearest, and I am hardly the type of woman to require smelling salts at the prospect of seeing a man naked. No, indeed. Rather, I should take much pleasure in the contemplation of your nudity, my dear. You were always such an - impressive - specimen of manhood."

Grim-faced, and flushed with self-consciousness, Sebastian begins to undress, folding his jacket over the armchair, before undoing his tie, and unbuttoning his waistcoat, collar and braces. His undershirt follows the previous items of clothing to the neat pile beside him. Only when he has kicked off his boots does he hesitate, his fingers fumbling over his fly buttons. 

He gasps as the Professor swats his backside unexpectedly with one of his metal slide rules. "Come on, Colonel. We have much to do and I do not wish to keep Miss Winter or, indeed, the ostler, waiting any longer than is strictly necessary."

Gritting his teeth, Sebastian undoes the last button, and slides his trousers, underwear and socks down in one fluid movement, before stooping to pull them off and adding them to the clothing pile. Then he stands, somewhat hunched forward, struggling with himself not to cross his hands over his genitals as the Professor and Kitty assess his naked body.

Kitty walks over and smiles up at him. "Well, Sebastian, I confess that I am most impressed. You look as fine an exemplification of masculinity as when we were together. You appear to have hardly aged a day or gained a pound in weight. Alas, if only Father Time would be as generous to me. I feel positively _haggard_ in comparison."

Sebastian inhales sharply. "What? You must be bloody jokin', Kitty. You look as lovely as ever I remember you lookin'. Radiant, you are, and - well, umm - lovely!"

He gasps as he receives another sharp smack to the backside with the slide rule. "Language, Colonel, even if I must say that I agree with your sentiments."

Kitty looks sideways at the Professor, a mischievous smile playing at the edge of her lips. "May I, Professor? For old times sake? He looks so very _delectable_."

At first, Sebastian thinks that the Professor will refuse to let her touch his tiger, his eyes slightly closed and lips pursed in silent contemplation, and his gaze cool. Then, suddenly, it is as if a ray of sunlight has illuminated his features and he smiles. 

"Oh yes, my dear. I rather think that this game may be rather more - interesting - with an additional player. Interesting for you and me, certainly. But whether our dear Sebastian will agree with us, we shall have to wait and see."


	6. Chapter 6

The Professor settles himself down in his favourite armchair, relishing the prospect of watching his tiger's discomfort at being _handled_ by Miss Winter. Moriarty has little time for women, usually, finding them far too silly, or vapid, or demanding, or doing such stupid things as falling in love with his nemesis, the insufferable Holmes. Well, that considerable _faux pas_ ended badly for the lady in question, did it not?

But Miss Winter he rather likes. She is witty and intelligent, and _self-contained_. She does not complain and she is not vexatious; she simply does what needs to be done with the minimum of fuss and annoyance. The good Colonel trusts her implicitly, and trusts her judgement, and God knows Moran's trust and confidence are extremely hard won. 

Besides, he knows of Moran's past with Kitty - knows that they were lovers, knows that they were _in love_ \- and that Moran is fond of her and quite animated, for such a generally quiet and careful man, in her company. And, perhaps most importantly, he knows that Sebastian, no matter what his alliances, loyalties and loves in the past, is now most immutably _his_ , and always will be. All of which leave the Professor in no doubt that Miss Winter is a most benevolent and congenial factor in his relationship with his sweet dove.

oOo

"We have an afternoon of physical endeavour before us, my dear Miss Winter, and I therefore see no reason why the good Colonel should not perhaps be _warmed up_ in preparation. What did you have in mind?"

Kitty circles Sebastian, a predatory smile on her face. "Dear Professor, when Sebastian and I were _intimate_ , he was always so very _masterful_ , so very _dominant_ , in our encounters. Not that I am raising any complaint about that - no! My goodness, far from it. But it would be so very delicious to turn the tables on your _tiger_ , to let him taste the authority of a _Mistress_. I doubt that Sebastian has ever submitted in any way to one of my sex, and I should very much savour the opportunity to remedy that, and be the first to do so."

Standing silent until now, whilst Moriarty and Kitty discuss him as if he were not present, Sebastian lets out a gasp at Kitty's words. He would never have thought, previously, of being in any way the submissive partner in an erotic encounter, but his relationship with the Professor has turned that rubric completely upon its head. Which is no doubt why his traitorous cock is twitching against his thigh at the prospect of being ordered by Kitty to do - what?

_Anything_ , his equally treacherous libido replies. _Anything Kitty desires of you_.

oOo

"Oh, Sebastian, my _darling_ , how eager you are! Professor, I should very much like to redden those _delectably_ muscular buttocks with a spanking. May I? Please? Only my hands may be too small to administer a _proper_ spanking, and so I wonder if you have anything that may assist me in warming Sebastian's backside in readiness for this afternoon?" 

The Professor moves to the desk and unlocks a drawer, retrieving a thick leather tawse. "I would imagine that this will assist, my dear. Now, Colonel, you will assume the position I have designated for a spanking, and present your _arse_ for Miss Winter's pleasure."


	7. Chapter 7

Sebastian complies, his face crimson with embarrassment, not only at having to assume such a humiliating position, but also at the fact that his cock has again sprung up to attention so readily. 

Kitty smiles. “My dearest Sebastian, if I had known that you would be so excited at the prospect of being used in such a way, I should have done this a long time ago.”

She strokes his buttocks and flanks soothingly, as if calming a wild beast which, in a way, Sebastian so closely resembles. He is all muscle and sinew and scars, tension pulled taut just below that creamy, freckled skin, quivering with anticipation of what is to come.

Kitty brings the tawse down hard on Sebastian’s upturned backside, provoking a gasp of surprise from the man below her.

“Bloody hell, Kitty! You ain’t half got one hell of an arm on you. That was a bloody belter!”

The Professor cuts in. “Colonel, you will be quiet as Miss Winter punishes you. You may gasp, and moan, and _beg_ , but otherwise you do not speak. Is that clear?”

Sebastian nods, and lowers his head as Kitty continues the beating. "I should imagine that he begs very prettily, does he not, Professor?"

Only when his arse is crimson, and Sebastian is whimpering and squirming at each stroke, does Kitty desist, again stroking the hot flesh gently, tickling at the back of Sebastian’s testicles with her fingertips, provoking more low moans. “You are quite lovely, dearest, and make me quite envious of the Professor. He is a very fortunate man to have snared himself such a magnificent creature.”

Moriarty chuckles. “I confess to being a rather selfish man, my dear, and do not in general ever share my – possessions – however, in your case I am prepared to make the occasional exception. Such as now; Colonel, up, if you please. We have to prepare you for your riding lesson.”

oOo

Sebastian breathes rapidly, the corset constricting his torso allowing only shallow breaths. The Professor and Kitty have laced him up far too bloody tightly, determined between them to give him at least the semblance of an hourglass figure. And the corset is not the only humiliation; his legs are encased in soft silk stockings, held up by the lacy, beribboned garters above his knees. 

The final indignity is the knickers, an abomination of silk, satin and lace, snug around his crotch, provoking yet another involuntary erection. Between them, the Professor and Kitty appear to have succeeded with their ministrations in inducing in him a near constant state of priapism.

“And, now, the _coup de grâce_. Your riding habit, Colonel.” Moriarty picks up the softly rustling silk dress, displaying it for Sebastian to take in. It is dark green silk, fashionably tight-bodiced with a high neck and tight sleeves, with a matching riding jacket, tailored into the waist, with short, flared tails at the back. The outfit is completed by a pair of black leather riding gloves and a black silk top hat with a heavy veil.

Sebastian sighs in resignation as the Professor gestures for him to step into the dress. It is very tight, fitting snugly over the corset, and Sebastian feels even more constricted once the dress has been buttoned right up to the high neck.

"Hmmm. That neckline is high enough for you to wear your collar underneath, Colonel." Seeing Kitty's eyes widen in surprise, the Professor continues. "Oh yes, Miss Winter. He has a variety of collars, and leashes. As you can see, he is an extremely well-trained tiger, but even the best behaved pets need putting in their place occasionally."

At Sebastian's strangled snort of indignation, Moriarty slips the riding jacket over the dress and buttons it. "There now, _pet_ , you are the epitome of the well-formed English horsewoman. Put on your hat and veil, and we shall be off!"


End file.
